M. Paris et al., SYNTHESIS OF N-CHAIN AND SIDE-CHAIN PROTECTED ASPARTYL AND GLUTAMYL ALDEHYDE DERIVATIVES - REINVESTIGATION OF THE REDUCTION OF WEINREB AMIDES, Tetrahedron letters, 39(11), 1998, pp. 1341-1344
The reduction of Weinreb amides was reinvestigated in order to find co
nditions that will allow the synthesis of protected aspartyl and gluta
myl aldehydes derivatives useful for peptide and pseudopeptide synthes
es. We have demonstrated that lithium tris(tert-butoxy)aluminium hydri
de [LiAl(OtBu)(3)H] and lithium tris[(3-ethyl-3-pentyl)oxy]aluminium h
ydride (LTEPA) can be used to reduce Weinreb amide derivatives into th
eir corresponding aldehydes. In these conditions, it was possible to s
ynthesize N- and side chain protected aspartyl and glutamyl aldehyde d
erivatives in fairly good conditions. (C) 1998 Elsevier Science Ltd. A
ll rights reserved.